Are we assuming that everyone is calling 'chili powder' just dried ground chilis? Otherwise, it's the blend of chilis and spices used to make 'chili' -- and varies from hot to mild, may have salt included. There is not strict guide to usage.

In this reporter's opinion chipotle has moved to the top of the list as most missued and abused ingredient in American cooking. It's now ahead of "balsamic" vinegar and sundried tomatoes on the chump chain of your supermarket shelf. Chipotle is smoked jalapeno, and no Bobby Flay, it doesn't taste like a spicy raisin.

My guess would be it depends on the chili powder and the chipotle powder. Different chili powders have different heats, so I almost always go by taste while I cook - or even try a bit of the chili powder before I start. Are you making a recipe you can taste as you go along, or try at the end and add more if necessary? If so, you can always start small and work your way up to the amount of heat you want.

chili powder is pretty much a generic term encompassing powders made from chilies across the scofield scale, Chipotle tends to be associated with a smoky quality, that others are not the heat thereof could be anywhere in between the ranges...
As for a raisin smell, not sure, but of late I seem to love smelling the fruity aroma that arises from a just open container of dried red chilies, (Don't over do it, the painful acridity is never far behind!!)

I'm going to assume you're buying these chili powders and chipotle powder in the USA, where the jars of spices labeled "Chili Powder" are usually powdered red chili (usually cayenne), salt, garlic powder, other spices, often including cumin and oregano, anti-caking agents and sometimes even dextrose (a sugar). So I'd start with a bit less chipotle powder than chili powder called for, as chili powder has a lot of fillers.

NO, not close to the same thing. You could, however, make your own chile powder using Chipotle powder (which is simply powdered, smoked Jalapenos, seeds, veins and all- very hot) for an unusual touch. It should be mostly powdered chiles- Ancho, maybe New Mexico or California- perhaps some Guajillo (or Negro)- whatever. And a good helping of cumin and oregano. Mexican oregano is to be preferred- it is from a completely different plant (Lippia Graveolens) than European oregano (Origanum Vulgare), and is quite different. Maybe a touch of allspice or cinnamon. This would allow you to skip the powdered onion and garlic that ruins most commercial chile powders.